Back in the days when hats--not handbags--were the crucial status accessory, women started think about their spring ones long before Easter.  And, while there’s still a nod to fancy millinery on 5th Avenue in New York city on Easter Sunday every year, these days May is when hat season truly begins.
In fact, as far as fancy hats go , this is probably the biggest month:  There’s this Saturday’s Kentucky Derby; Cinco De Mayo;

and, of course, all those afternoon weddings and graduations,

not to mention the occasional “Hookers & Johns” -themed polo match.

It’s also when we tend to focus on those everyday hats we all depend upon to protect us against the Florida sun’s ever-more-brutal rays.  After all, sunscreen can only do so much, Darlings; if you don’t want that glycolic peel to backfire or those expensive highlights to turn to brass, you’re most certainly going to need to wear something on your head besides sunglasses.

We’ve seen all kinds of great hats this season, but the one thing that’s definitely OUT is the baseball-cap-with-the-ponytail-pulled-through-the-hole-in-the-back look. 
Unless you’re still wearing tracksuits and crop tops and Jessica Simpson is your favorite fashion icon,

(in which case, you’re in more trouble than you know), you probably want to give the cap a rest and try something new this season.

So what’s hot now?  While the trim little bucket hat that’s been so popular for the past few seasons can still be found, it seems to be losing ground to wider-brimmed hats, especially straw models in all shapes and weaves, like the ones InStyle magazine features on page 178 of their May issue:

But whether it’s straw or fabric, the best style for you will depend on your age, taste, budget, plus how worried you are about looking stupid.  (Let’s face it, as far as accessories go, hats are notoriously hard to pull off, and, unless you’re, say, Isabella Blow, it may take you a while before you find one that doesn’t make you feel self-conscious.)  

Dramatic types can opt for the super-wide brims like this one Michael Kors featured in his Spring 2008 collection,

and which can be found in all price ranges; from the pricey high-end brands like this $325 Eric Javits,

along with Helen Kaminski, and Juicy Couture (at Nordstrom, Saks, and Nieman’s); Burberry (at Saks and Neiman’s); Kokin (at Neiman’s); and Brooks Brothers, (at Brooks Brothers); to a $9.99 version from K Mart. 

But we think the best values in this category are in the mid-range;  despite its relatively modest price tag, Ann Taylor‘s $48 structured black straw is rawther Royal Ascot, don’t you think?

And Banana Republic‘s $52 natural straw version

has a definite San Tropez vibe.

For something just as showy but a little more unique, Anthropologie’s Audrey Hepburn-looking hats, like this $88 “Yucca”

or the “Cabrillo" for $58 would be at home in any chi-chi resort on the right kind of head.

If you’re more inclined to go with a not-so-extreme, medium-brimmed look (our favorite is other one from Michael Kors Spring 2008 collection):

J. Crew‘s $50 straw hat is a perfectly proportioned interpretation of a classic:

(As usual!). 

J. Crew also has some great fabric hats in fun prints for around $35, but we like the $10 price of the cute prints like this one from the Cynthia Rowley Whim collection for Target,

or this cute rib-stitched for $20 from JC Penney:



For the young and/or trendy, it’s fedoras, bowlers, and straw cowboy hats that are the most popular with the cool kids.


Straw cowboy hats like this $20 one from South Moon Under

have been a favorite of Hollywood bimbo-types like Denise Richards for years,

and they’re still a great casual look, especially when you pair one with, say, a sundress or a gauzy tunic.

For more edge, try a straw fedora like like Sienna Miller’s

Ashlee Simpson’s,

and even--albeit in one of her saner moments--Britney’s;

(the blonde one, not her brunette British alter-ego/evil twin)

or a bowler like Mischa Barton’s

or Kiera Knightly’s.

(Don’t ask us what that Jiffy-Pop thing on Rupert Friend’s head is).



Both can be found for cheap ($28, to exact) at Urban Outfitters:

And if you still haven’t found what you’re looking for, browse the
hat section of InStyle’s shopping guide, where you’ll find every kind of hat imaginable, plus a few more.

But whatever you do, just remember to stay away from…

well, you know.